Stereodivergent Pd/Cu catalysis: asymmetric alkylation of racemic symmetrical 1, 3-diphenyl allyl acetates. Issue 9 (18th February 2021)

• Record Type: Journal Article
• Authors: Zhao, Ling; Li, Guanlin; He, Rui; Liu, Penglin; Wang, Feijun; Huo, Xiaohong; Zhao, Min; Zhang, Wanbin
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 9(2021)
• Page Start: 1955
• Page End: 1959
• Publication Date: 2021-02-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob02499f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A stereodivergent Pd/Cu catalyst system was developed, which was successfully applied to the asymmetric allylic alkylation of symmetrical 1, 3-disubstituted allyl acetates with prochiral imino esters in a fully stereodivergent manner. Abstract : We report a stereodivergent Pd/Cu catalyst system that was successfully applied to the asymmetric allylic alkylation of symmetrical 1, 3-disubstituted allyl acetates with prochiral imino esters, providing efficient access to enantiopure products bearing vicinal stereocenters in a fully stereodivergent manner. The protocol proceeds smoothly under mild reaction conditions and can accommodate a range of imino esters, delivering the substituted products in high yields and with excellent diastereoselectivities (up to >20 : 1 dr) and enantioselectivities (up to >99% ee).